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Communications issues are usually two-sided so I'd lean more heavily towards figuring out what those could be. 30 people split between 3 timezones is challengin

Communications issues are usually two-sided so I'd lean more heavily towards figuring out what those could be. 30 people split between 3 timezones is challenging. 1) Ask why the other person is leaving for real. They should be vulnerable and tell you the truth. Sometimes they'll hide behind something like "thats confidential" which you can't really argue with, but I'd dig into it. If they get nervous walk away. 2) Ask them what systems or processes they want to improve or change and why. What isn't working? etc. 3) How will you be evaluated in your role. Sometimes there are unclear expectations from managers or any other "leadership" style role at a company. This isn't OK because it might just take one person to change their mind about how you're doing for you to be "not good enough". Again; dig into it. 4) How is the company doing from a financial perspective. Whats the burn? Whats the revenue? What's the LTV/CAC? If they can't answer or won't, I'd consider that a red flag. 5) How is the product roadmap set. How far out are they thinking? Make sure it lines up with your vision of how to organize groups the right way.

ryandrake 10y ago
> 3) How will you be evaluated in your role. Sometimes there are unclear expectations from managers or any other "leadership" style role at a company. This isn't OK because it might just take one person to change their mind about how you're doing for you to be "not good enough". Again; dig into it. This one is key. Good answer is: "You will have these N observable, measurable KPIs. Good performance means meeting them, excellent performance means exceeding them by P%, etc." Bad answer is if they can't tell you or anything subjective (Your manager vaguely "evaluates" your performance each year). > 4) How is the company doing from a financial perspective. Whats the burn? Whats the revenue? What's the LTV/CAC? If they can't answer or won't, I'd consider that a red flag. I've seen business owners take great offense to being asked about these "company health" type questions. Often due to the answer not being pretty. As if I, as a potential employee, am not a stakeholder. If they get cagey about this it's definitely a red flag.

ryandrake 10y ago

> 3) How will you be evaluated in your role. Sometimes there are unclear expectations from managers or any other "leadership" style role at a company. This isn't OK because it might just take one person to change their mind about how you're doing for you to be "not good enough". Again; dig into it. This one is key. Good answer is: "You will have these N observable, measurable KPIs. Good performance means meeting them, excellent performance means exceeding them by P%, etc." Bad answer is if they can't tell you or anything subjective (Your manager vaguely "evaluates" your performance each year). > 4) How is the company doing from a financial perspective. Whats the burn? Whats the revenue? What's the LTV/CAC? If they can't answer or won't, I'd consider that a red flag. I've seen business owners take great offense to being asked about these "company health" type questions. Often due to the answer not being pretty. As if I, as a potential employee, am not a stakeholder. If they get cagey about this it's definitely a red flag.